2-Aminothiophenol → HCID 178420811, compound

Participants

Reaction Steps

To a solution of 3-(3-(tetrahydro-2H-pyran-4-yl)pyridin-2-yloxy)cyclobutanecarboxylic acid (prepared according to Scheme 4) (0.236 g, 0.851 mmol) in DCM (0.5 mL) at RT was added DMF (1 drop) and oxalyl dichloride (0.50 mL, 5.6 mmol). The reaction mixture was stirred at RT for 10 min and the solvent was removed under reduced pressure. The concentrate was dissolved in toluene (3 mL), cooled to 0° C., and 2-aminobenzenethiol (0.10 mL, 0.94 mmol) was added. The reaction mixture was warmed to RT and stirred for 2 h. The reaction was neutralized with saturated NaHCO3 and diluted with EtOAc. The organic phase was washed with water (1×), brine (1×), dried over MgSO4, filtered, and concentrated. Purification by flash column chromatography on silica gel (5% to 30% EtOAc in hexanes) followed by purification by flash column chromatography on silica gel (5% to 30% DCM in hexanes) gave 2-(trans-3-(3-(tetrahydro-2H-pyran-4-yl)pyridin-2-yloxy)cyclobutyl)benzo[d]thiazole (0.018 g, 0.049 mmol, 6% yield) and 2-(cis-3-(3-(tetrahydro-2H-pyran-4-yl)pyridin-2-yloxy)cyclobutyl)benzo[d]thiazole (0.029 g, 0.079 mmol, 9% yield) as colorless oils. [M+1]=367 each. IC50 (uM): 0.01497 (trans) and 0.0633 (cis).

Provenance & Evidence